Methyl Salicylate → Methyl 2-(2-chloroethoxy)benzoate

HRID 457778

Reaction equation

HRID 457778 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:16][CH3:17])(=[O:15])[C:8]1[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[OH:10].Br[CH2:19][CH2:20][Cl:21]>C(C(C)=O)C>[CH3:17][O:16][C:7](=[O:15])[C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[O:10][CH2:19][CH2:20][Cl:21]

Participants

5

Reactant 3

HCID 4133Methyl SalicylateHCID 78491-Bromo-2-Chloroethane2×HCID 11430Potassium Carbonate2×

Product 1

HCID 9837283Methyl 2-(2-chloroethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

34 g (0.25 mol) of potassium carbonate were added to a solution of 25 g (0.16 mol) of methyl salicylate in 250 ml of methyl ethyl ketone. This mixture was refluxed for 1 h, then 27.3 ml (0.35 mol) of 1-bromo-2-chloro-ethane were added and the mixture was taken to reflux again. Four hours later, 34 g (0.25 mol) more of potassium carbonate and 16.3 ml (0.2 mol) more of 1-bromo-2-chloro-ethane were added. This operation was repeated until the reaction was completed. The inorganic salts were filtered off and the liquid phase was diluted with the same volume of hexane. This organic phase was washed twice with water and worked-up as usual. The yield in this step was quantitative and the product was pure enough for the next synthetic step.

Workup

  1. temperatureThis mixture was refluxed for 1 h
  2. temperatureto reflux again
  3. filtrationThe inorganic salts were filtered off
  4. additionthe liquid phase was diluted with the same volume of hexane
  5. washThis organic phase was washed twice with water
  6. customThe yield in this step

Sources & evidence

ORD record
ord-9aabaa3017474a3ca3687eecadcc13ca
Source dataset
uspto-grants-2007_03
Patent number
US07189741B2

Linked notes

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